Thebainone
Title: Thebainone
CAS Registry Number: 467-98-1
CAS Name: 7,8-Didehydro-4-hydroxy-3-methoxy-17-methylmorphinan-6-one
Additional Names: thebainone-A
Molecular Formula: C18H21NO3
Molecular Weight: 299.36
Percent Composition: C 72.22%, H 7.07%, N 4.68%, O 16.03%
Literature References: Prepn from thebaine, codeinone or b-ethylthiocodide: Morris, Small, J. Am. Chem. Soc. 56, 2159 (1934). Earlier references and discussion of structure: Small, Lutz, "Chemistry of the Opium Alkaloids" in U.S. Public Health Reports Suppl. No. 103 (Washington, 1932). About anomalies in nomenclature and difference from metathebainone see Henry, Plant Alkaloids (London, 1939) p 249. Description of all thebainones: K. W. Bentley, The Chemistry of the Morphine Alkaloids (Oxford, 1954) p 219.
Properties: Crystals from ethyl acetate, mp 146°. [a]D28 -47° (c = 1.16 in 95% alc). One gram dissolves in 250 ml water, about 120 ml boiling water. Sol in chloroform, benzene, acetone; sparingly sol in ether, alcohol, methanol.
Melting point: mp 146°
Optical Rotation: [a]D28 -47° (c = 1.16 in 95% alc)
 
Derivative Type: Sesquihydrate
Properties: Crystals from water, mp 90°.
Melting point: mp 90°
 
Derivative Type: Methanolate
Properties: Crystals from methanol, mp 118°.
Melting point: mp 118°
 
Derivative Type: Hydrochloride
Molecular Formula: C18H21NO3.HCl
Molecular Weight: 335.83
Percent Composition: C 64.38%, H 6.60%, N 4.17%, O 14.29%, Cl 10.56%
Properties: Crystals from alcohol, mp 256° (turns red at mp). [a]D30 -25° (c = 1.63).
Melting point: mp 256° (turns red at mp)
Optical Rotation: [a]D30 -25° (c = 1.63)
 
Derivative Type: Hydriodide
Molecular Formula: C18H21NO3.HI
Molecular Weight: 427.28
Percent Composition: C 50.60%, H 5.19%, N 3.28%, O 11.23%, I 29.70%
Properties: Crystals, mp 165°, solidifies and remelts 260°.
Melting point: mp 165°
 
Derivative Type: Methiodide
Properties: mp 251°.
Melting point: mp 251°

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